Synthesis of spiro[indoline-3,2′-quinoline] derivatives through a four-component reaction

Article abstract of DOI:10.1002/ejoc.201101737

An efficient synthetic procedure for the synthesis of functionalized tetrahydrospiro[indoline-3,2′-quinoline] derivatives was successfully developed and involves the four-component reaction of arylamines, dimethyl acetylenedicarboxylate, isatins, and a cyclohexane-1,3-dione in acetic acid. The advantages of this reaction include the use of common starting materials and mild reaction conditions and it is operationally simple. An efficient synthetic procedure for the synthesis of functionalized tetrahydrospiro[indoline-3, 2′-quinoline] derivatives was successfully developed and involves the four-component reaction of arylamines, dimethyl acetylenedicarboxylate, isatins, and a cyclohexane-1,3-dione in acetic acid. Copyright

Full text of DOI:10.1002/ejoc.201101737

FULL PAPER
DOI: 10.1002/ejoc.201101737
Synthesis of Spiro[indoline-3,2Ј-quinoline] Derivatives through a
Four-Component Reaction
Jing Sun,[a] Yan Sun,[a] Hong Gao,[a] and Chao-Guo Yan*[a]
Keywords: Multicomponent reactions / Alkynes / Heterocycles / Spiro compounds
An efficient synthetic procedure for the synthesis of function-
alized tetrahydrospiro[indoline-3,2Ј-quinoline] derivatives
was successfully developed and involves the four-component
reaction of arylamines, dimethyl acetylenedicarboxylate, is-
atins, and a cyclohexane-1,3-dione in acetic acid. The advan-
tages of this reaction include the use of common starting ma-
terials and mild reaction conditions and it is operationally
simple.
1,4-dipoles derived from the reaction of electron-deficient
alkynes with primary arylamines and developing new multi-
component reactions for the synthesis of heterocyclic com-
pounds,[22,23] herein we wish to report the efficient synthesis
of functionalized spiro[indoline-3,2Ј-quinoline] derivatives
through the four-component reaction of arylamines, acet-
ylenedicarboxylate, isatins, and cyclohexane-1,3-dione.
Introduction
The spirooxindole system is the core structure of many
pharmacological agents and natural alkaloids.[1,2] Spiro-
oxindoles, especially those spiroannulated with heterocycles
at the 3-position, have shown good biological activities.[3]
These potential properties have prompted many efforts to-
ward the synthesis of spirooxindole-fused heterocycles, and
numerous impressive successes have been obtained for the
synthesis of diversely structured spirocyclic oxindoles.[4,5]
Isatin is probably one of the most widely used reagents for
the construction of spirooxindoles and has been used in
many reactions such as 1,3-dipolar cycloadditions,[6–8] Mor-
ita–Baylis–Hillman reactions,[9,10] and other condensation
reactions.[11] In the past few years, multicomponent reac-
tions based on the versatile reactivity of isatins have become
efficient methods for the synthesis of various spirooxin-
doles.[12–16] On the other hand, the diverse reactivity of
Huisgen 1,4-dipoles, which are easily formed from the ad-
dition reaction of nitrogen heterocycles to electron-deficient
alkynes, has been widely used in multicomponent reactions
to develop a number of carbon–carbon bond formation re-
actions and heterocyclic constructions.[17,18] Recently, sev-
eral multicomponent reactions based on the sequential re-
actions of the initially formed Huisgen’s 1,4-dipoles with
isatins[19] or benzofuran-2,3-diones[20] have become efficient
synthetic procedures for constructing versatile spirooxind-
ole systems. Perumal and co-workers successfully reported
the synthesis of spiro[indole-3,4Ј-pyridine] derivatives
through a four-component reaction of arylamine, acetylene-
dicarboxylate, an aromatic aldehyde, and isatin.[21] As part
of our program on the study of the reactivity of Huisgen’s
Results and Discussion
In an initial study, p-methoxyaniline was treated with di-
methyl acetylenedicarboxylate in acetic acid to give the
active intermediate β-enamino ester according to our pre-
viously established procedure.[22] Then, isatin and dimedone
were added, and the mixture was stirred at ambient tem-
perature overnight. After workup, a yellow solid was ob-
tained in about 40% yield after separation by preparative
thin-layer chromatography. Its structure was assigned as un-
usual
tetrahydrospiro[indoline-3,2Ј-quinoline]-2,5Ј-dione
(1a) and not the expected normal spiro[indoline-3,4Ј-quin-
oline] derivative (Scheme 1) according to the results of the
reported multicomponent reactions containing isatin.[15,21]
From the molecular structure of spiro compound 1a it is
clear that the β-enamino ester is absent in the final product,
whereas the amino group of the arylamine is bridged be-
tween the isatin and dimedone molecules. In a second ex-
periment, the three-component reaction of dimethyl acet-
ylenedicarboxylate, dimedone, and isatin imine, which was
prepared in situ from the reaction of p-methoxyaniline with
isatin, was performed (Scheme 1). This three-component re-
action also resulted in the formation of 1a in a similar yield.
In the next experiment, the four-component mixture of p-
methoxyaniline, dimethyl acetylenedicarboxylate, isatin,
and dimedone in acetic acid was run at ambient tempera-
ture overnight to give spiro compound 1a in 46% yield.
These results indicate that a one-pot four-component reac-
tion could be established for the preparation of function-
alized tetrahydrospiro[indoline-3,2Ј-quinoline]-2,5Ј-diones.
[a] College of Chemistry & Chemical Engineering,
Yangzhou University,
Yangzhou 225002, China
E-mail: cgyan@yzu.edu.cn
Supporting information for this article is available on the
WWW under http://dx.doi.org/10.1002/ejoc.201101737.
1976
© 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Eur. J. Org. Chem. 2012, 1976–1983

Synthesis of Spiro[indoline-3,2Ј-quinoline] through a 4CR
Scheme 1. Synthetic routes to tetrahydrospiro[indoline-3,2Ј-quinoline] (1a).
Having achieved inspiring results from the four-compo- single-crystal X-ray diffraction studies performed for com-
nent reactions, we explored its cope and limitations. Under pounds 1e (Figure 1) and 1j (Supporting Information, Fig-
similar reaction conditions, various arylamines and isatins ure S1).
bearing a 5-methyl, 5-chloro, 1-benzyl, or 1-n-butyl group
and diethyl acetylenedicarboxylate were used in the four-
component reaction. All reactions proceeded smoothly at
room temperature, and the corresponding spiro derivatives
1b–q were prepared in moderate yields (Table 1). Products
1a–j were fully characterized by elemental analysis; 1H
NMR, 13C NMR, and IR spectroscopy; and mass spec-
trometry, and the structures were further confirmed by
Table 1. Synthesis of spiro[indoline-3,2Ј-quinoline]s 1a–q through a
four-component reaction.
Figure 1. Molecular structure of spiro compound 1e.
The preparation of tetrahydrospiro[indoline-3,2Ј-quinol-
Entry
1
Ar
R
RЈ
RЈЈ
Yield
[%]
ine]-2,5Ј-diones is very exciting. In the literature, there are
several multicomponent reactions containing isatin, cyclic
1,3-diketones, and aminoheterocycles, which give spiro-
[indoline-3,4Ј-quinoline] derivatives as main products.[15,21]
However, to the best of our knowledge, there are very few
synthetic methods for the preparation of the isomeric spiro-
[indoline-3,2Ј-quinoline] system.[16] Thus, our present pro-
tocol provides an efficient synthetic procedure for the prep-
aration of spiro[indoline-3,2Ј-quinoline] derivatives. To
broaden the scope of this four-component reaction, similar
reactions containing cyclohexane-1,3-dione were also car-
ried out and spiro[indoline-3,2Ј-quinoline] derivatives 2a–l
were prepared in good yields (Table 2). Their structures
were established on the basis of spectroscopic data and sin-
gle-crystal structure determination of spiro compounds 2e
(Figure 2) and 2k (Supporting Information, Figure S2).
1
2
3
4
5
6
7
8
1a p-CH3OC6H4
1b
1c
1d p-CH3OC6H4
1e
1f
CH3
CH3
CH3
CH3
CH3
CH3
CH3
CH3
CH3
CH3
H
H
H
CH3
CH3
CH3
CH3
CH3
Cl
Cl
H
Cl
H
H
H
H
H
H
H
H
H
H
H
H
H
H
46
42
43
52
49
42
42
53
55
40
50
60
55
C6H5
p-ClC6H4
p-CH3C6H4
m-CH3C6H4
C6H5
1g
1h
p-ClC6H4
9
1i p-CH3OC6H4
1j
1k
10
11
12
13
14
15
16
17
C6H5
p-CH3C6H4 CH2CH3
1l p-CH3OC6H4 CH2CH3
1m
1n
p-ClC6H4
p-CH3C6H4
CH2CH3
CH3
H
CH2C6H5 61
1o p-CH3OC6H4 CH2CH3 CH3 CH2C6H5 67
1p
1q
p-CH3C6H4
p-ClC6H4
CH3
CH3
Cl
CH3
n-C4H9
n-C4H9
65
70
Eur. J. Org. Chem. 2012, 1976–1983
© 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
www.eurjoc.org
1977

J. Sun, Y. Sun, H. Gao, C.-G. Yan
FULL PAPER
Table 2. Synthesis of spiro[indoline-3,2Ј-quinoline] 2a–l through a This mechanism was partially supported by the two one-
four-component reaction.
pot three-component reactions described in Scheme 1. In
situ formed isatin imine B reacted with dimedone and di-
methyl acetylenedicarboxylate to result in spiro compound
1. On the other hand, if the β-enamino ester derived from
the reaction of acetylenendicarboxylate and the arylamine
reacted further with isatin and dimedone, the main product
was still spiro compound 1, because the β-enamino ester
was in equilibrium with acetylenendicarboxylate and the
arylamine in solution. Attempts to isolate intermediate A
were not successful, and A was quickly converted into hexa-
hydro-1-benzofuran-2,3-dicarboxylate through intramolec-
ular Michael O-alkylation of the enolate to the C=C
bond.[24] Alternatively, a reaction mechanism involving an
imino-Diels–Alder reaction[25] might also be possible, in
which intermediate A is converted into its enol form, and
then the Diels–Alder reaction takes place between the enol
and imine B. It is a pity that our results cannot distinguish
between these two mechanisms at this time.
Entry
2
Ar
R
RЈ
RЈЈ
Yield
[%]
1
2
3
4
5
6
7
8
2a
2b
2c
2d
2e
2f
2g
2h
2i
p-CH3OC6H4
p-CH3C6H4
C6H5
CH3
CH3
CH3
CH3
CH3
CH3
CH3
CH3
CH3
CH3
CH3 CH2C6H5
CH2C6H5
CH3 CH2C6H5
72
62
53
60
67
61
70
64
59
72
51
78
H
p-ClC6H4
H
CH2C6H5
n-C4H9
n-C4H9
n-C4H9
n-C4H9
n-C4H9
n-C4H9
p-CH3OC6H4
p-CH3C6H4
p-CH3OC6H4
p-CH3C6H4
p-ClC6H4
m-NO2C6H4
p-ClC6H4
CH3
CH3
F
Cl
CH3
CH3
9
10
11
12
2j
2k
2l
CH2CH3 CH3 CH2C6H5
p-CH3C6H4 CH2CH3 CH3
H
Figure 2. Molecular structure of spiro compound 2e.
Scheme 2. Mechanism for the formation of tetrahydrospi-
ro[indoline-3,2Ј-quinoline]-2,5Ј-dione.
Although the exact mechanism of this reaction is not
very clear at present, a plausible mechanism for the forma-
tion of spiro[indoline-3,2Ј-quinoline]s (Scheme 2) is pre-
sented on the basis of the analysis of similar multicompo-
nent reactions of isatin[15,19] and our recently reported prep-
Conclusions
In summary we have developed a four-component reac-
aration of fused 1,2-dihydropyridines through a domino re- tion for the efficient synthesis of functionalized tetrahydro-
action involving arylamines, acetylenedicarboxylate, aro- spiro[indoline-3,2Ј-quinoline]s. The available diversity of
matic aldehydes, and dimedone.[23] Firstly, reaction of di- each of the components used in the four-component reac-
medone with dimethyl acetylenedicarboxylate in acetic acid tions enables a wide range of substrates to be prepared with
forms adduct A, which has been described in several re- a broad range of physical properties. Furthermore, this re-
ports.[24] Secondly, the reaction of isatin with an arylamine action has several advantages including the use of common
in acetic acid forms isatin imine B. Then, Michael addition starting materials and mild reaction conditions and it is op-
of intermediate A to imine B affords adduct C. Thirdly, in- erationally simple. Potential uses of the reaction in synthetic
tramolecular condensation of the amino group with the and medicinal chemistry might be quite significant. Further
carbonyl group in intermediate C affords tetrahydrospi- expansion of the reaction scope and synthetic applications
ro[indoline-3,2Ј-quinoline]-2,5Ј-dione 1 after dehydration. of this methodology are in progress in our laboratory.
1978
www.eurjoc.org
© 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Eur. J. Org. Chem. 2012, 1976–1983

Synthesis of Spiro[indoline-3,2Ј-quinoline] through a 4CR
C30H30N2O7 (530.58): calcd. C 67.91, H 5.70, N 5.28; found C
67.74, H 5.48, N 5.03.
Experimental Section
General Procedure for the Preparation of Spiro[indoline-3,2Ј-quin-
oline]-2,5Ј-diones 1a–q and 2a–l:
1e: Yellow solid, yield: 49%, m.p. 272–274 °C. 1H NMR (600 MHz,
CDCl3): δ = 7.35 (s, 1 H, ArH), 7.16 (br. s, 2 H, ArH), 7.05 (d, J
= 7.2 Hz, 1 H, ArH), 6.84 (d, J = 7.2 Hz, 1 H, ArH), 6.51–6.50
(m, 1 H, ArH), 6.11–6.09 (m, 1 H, ArH), 3.91 (s, 3 H, OCH3), 3.54
(s, 3 H, OCH3), 2.33–2.31 (m, 6 H, CH3), 2.27 (br. s, 2 H, CH2),
2.02–2.00 (m, 1 H, CH), 1.87 (d, J = 16.8 Hz, 1 H, CH), 0.96 (s, 6
H, CH3) ppm. 13C NMR (150 MHz, CDCl3): δ = 164.0, 139.6,
137.5, 134.9, 133.0, 131.4, 131.3, 130.3, 129.7, 129.3, 109.9, 70.7,
52.3, 51.9, 49.9, 42.7, 32.0, 28.3, 28.2, 28.1, 21.2, 21.1 ppm. IR
A solution of arylamine
(2.0 mmol), acetylenedicarboxylate (2.0 mmol), isatin (2.0 mmol),
and cyclic 1,3-diketone (2.0 mmol) in acetic acid (5.0 mL) was
stirred at room temperature for about 24 h. The resulting precipi-
tates were collected by filtration. This crude product was subjected
to preparative thin-layer chromatography (SiO2; ethyl acetate/light
petroleum, 1:3) and washed with ethanol to give the pure product
for analysis.
1a: Yellow solid, yield: 46%, m.p. 270–271 °C. 1H NMR (600 MHz,
CDCl3): δ = 7.81 (s, 1 H, NH), 7.53 (s, 1 H, ArH), 7.25 (br. s, 1 H,
ArH), 7.19–7.18 (m, 1 H, ArH), 7.06 (br. s, 1 H, ArH), 6.85–6.84
(m, 1 H, ArH), 6.63 (br. s, 1 H, ArH), 6.53–6.52 (m, 1 H, ArH),
6.12–6.11 (m, 1 H, ArH), 3.90 (s, 3 H, OCH3), 3.76 (s, 3 H, OCH3),
3.50 (s, 3 H, OCH3), 2.26 (s, 2 H, CH2), 2.03–2.00 (m, 1 H, CH),
1.88 (d, J = 16.8 Hz, 1 H, CH), 0.96 (s, 6 H, CH3) ppm. 13C NMR
(150 MHz, CDCl3): δ = 164.0, 159.8, 140.0, 131.3, 131.1, 130.9,
130.1, 123.4, 114.4, 114.0, 110.1, 55.4, 52.4, 52.0, 49.9, 42.7, 32.0,
(KBr): ν = 2950, 1748, 1707, 1601, 1493, 1431, 1380, 1302, 1197,
˜
1153, 1122, 1017, 855, 822 cm–1. MS: m/z (%) = 513.39 (100) [M –
1]+. C30H30N2O6 (514.58): calcd. C 70.02, H 5.88, N 5.44; found C
69.84, H 6.15, N 5.37.
1f: Yellow solid, yield: 42%, m.p. 274–276 °C. 1H NMR (600 MHz,
CDCl3): δ = 7.67 (d, J = 10.8 Hz, 1 H, NH), 7.34 (br. s, 1 H, ArH),
7.23 (t, J = 7.8 Hz, 1 H, ArH), 7.12–7.10 (m, 1 H, ArH), 7.05–7.04
(m, 2 H, ArH), 6.51 (br. s, 1 H, ArH), 5.99 (s, 1 H, ArH), 3.90 (s,
3 H, OCH3), 3.50 (s, 3 H, OCH3), 2.33–2.32 (m, 6 H, CH3), 2.27
(s, 2 H, CH2), 1.93–1.91 (m, 1 H, CH), 1.89–1.86 (m, 1 H, CH),
0.96 (s, 6 H, CH3) ppm. 13C NMR (150 MHz, CDCl3): δ = 164.1,
139.8, 138.7, 137.6, 137.5, 137.4, 137.3, 133.1, 133.0, 131.5, 131.3,
131.2, 130.4, 130.2, 130.1, 129.3, 128.4, 126.9, 109.8, 109.7, 52.4,
51.9, 49.9, 42.8, 42.7, 32.0, 28.3, 28.2, 28.1, 28.0, 21.3, 21.1,
28.4, 28.0 ppm. IR (KBr): ν = 2953, 1744, 1610, 1502, 1429, 1246,
˜
1206, 1133, 1105, 1019, 933, 856, 753 cm–1. MS: m/z (%) = 515.31
(100) [M – 1]+. C29H28N2O7 (516.55): calcd. C 67.43, H 5.46, N
5.42; found C 67.56, H 5.71, N 5.15.
1b: Yellow solid, yield: 42%, m.p. ~162–164 °C. 1H NMR
(600 MHz, CDCl3): δ = 7.93 (s, 1 H, NH), 7.56–7.55 (m, 1 H,
ArH), 7.38 (t, J = 7.2 Hz, 1 H, ArH), 7.32 (t, J = 7.2 Hz, 1 H,
ArH), 7.30–7.28 (m, 1 H, ArH), 7.26–7.24 (m, 1 H, ArH), 7.10–
7.05 (m, 2 H, ArH), 6.62–6.61 (m, 1 H, ArH), 6.23 (d, J = 7.2 Hz,
1 H, ArH), 3.91 (s, 3 H, OCH3), 3.52 (s, 3 H, OCH3), 2.28 (s, 2 H,
CH2), 2.01 (d, J = 16.8 Hz, 1 H, CH), 1.86 (d, J = 16.8 Hz, 1 H,
CH), 0.96 (s, 6 H, CH3) ppm. 13C NMR (150 MHz, CDCl3): δ =
176.0, 164.0, 139.8, 137.4, 131.2, 131.0, 130.0, 129.8, 129.6, 128.7,
21.0 ppm. IR (KBr): ν = 2951, 1746, 1707, 1625, 1600, 1492, 1431,
˜
1373, 1313, 1193, 1150, 1110, 1047, 1018, 831, 797 cm–1. MS: m/z
(%) = 513.34 (100) [M – 1]+. C30H30N2O6 (514.58): calcd. C 70.02,
H 5.88, N 5.44; found C 70.16, H 6.23, N 5.16.
1g: Yellow solid, yield: 42%, m.p. 266–268 °C. 1H NMR (600 MHz,
CDCl3): δ = 7.80 (s, 1 H, NH), 7.40–7.37 (m, 2 H, ArH), 7.34–7.32
(m, 1 H, ArH), 7.29–7.27 (m, 1 H, ArH), 7.08–7.05 (m, 2 H, ArH),
6.51 (br. s, 2 H, ArH), 6.23 (d, J = 7.8 Hz, 1 H, ArH), 3.92 (s, 3
H, OCH3), 3.53 (s, 3 H, OCH3), 2.33 (s, 3 H, CH3), 2.28 (s, 2 H,
CH2), 2.01 (d, J = 17.4 Hz, 1 H, CH), 1.87 (d, J = 17.4 Hz, 1 H,
CH), 0.96 (s, 6 H, CH3) ppm. 13C NMR (150 MHz, CDCl3): δ =
176.0, 164.0, 137.5, 137.3, 133.4, 131.4, 131.3, 130.1, 129.7, 129.5,
128.7, 109.9, 52.4, 52.0, 49.8, 42.8, 28.1, 21.1, 20.7 ppm. IR (KBr):
123.6, 110.2, 52.4, 52.1, 49.8, 42.8, 28.0, 20.7 ppm. IR (KBr): ν =
˜
2965, 1742, 1693, 1626, 1596, 1482, 1428, 1344, 1281, 1214, 1132,
1099, 1021, 890, 826, 765 cm–1. MS: m/z (%) = 485.34 (100) [M –
1]+. C28H26N2O6 (486.52): calcd. C 69.12, H 5.39, N 5.76; found C
68.75, H 5.53, N 5.68.
1c: Yellow solid, yield: 43%, m.p. 286–287 °C. 1H NMR (600 MHz,
CDCl3): δ = 7.71 (s, 1 H, NH), 7.55 (br. s, 1 H, ArH), 7.39–7.37
(m, 1 H, ArH), 7.31–7.24 (m, 2 H, ArH), 7.12–7.04 (m, 2 H, ArH),
6.67 (br. s, 1 H, ArH), 6.18 (br. s, 1 H, ArH), 3.91 (s, 3 H, OCH3),
3.54 (s, 3 H, OCH3), 2.30–2.28 (m, 2 H, CH2), 2.00 (br. s, 1 H,
CH), 1.86–1.84 (m, 1 H, CH), 0.97 (s, 6 H, CH3) ppm. 13C NMR
(150 MHz, CDCl3): δ = 164.0, 139.8, 135.9, 135.7, 135.6, 131.7,
131.6, 131.2, 130.9, 130.1, 129.0, 123.7, 110.3, 52.5, 52.2, 49.8, 42.8,
ν = 2953, 1742, 1697, 1624, 1597, 1488, 1430, 1385, 1342, 1298,
˜
1273, 1213, 1153, 1020, 828, 792, 761 cm–1. MS: m/z (%) = 499.40
(100) [M – 1]+. C29H28N2O6 (500.55): calcd. C 69.59, H 5.64, N
5.60; found C 69.27, H 5.92, N 5.40.
1h: Yellow solid, yield: 53%, m.p. 294–297 °C. 1H NMR (600 MHz,
CDCl3): δ = 7.37–7.34 (m, 3 H, NH, ArH), 7.25–7.23 (m, 1 H,
ArH), 7.07–7.04 (m, 2 H, ArH), 6.54–6.53 (m, 1 H, ArH), 6.18–
6.17 (m, 1 H, ArH), 3.91 (s, 3 H, OCH3), 3.55 (s, 3 H, OCH3), 2.33
(s, 3 H, CH3), 2.28 (s, 2 H, CH2), 1.99 (d, J = 17.4 Hz, 1 H, CH),
1.86 (d, J = 17.4 Hz, 1 H, CH), 0.97 (s, 6 H, CH3) ppm. 13C NMR
(150 MHz, CDCl3): δ = 164.0, 137.2, 136.0, 135.7, 133.5, 131.7,
131.6, 131.0, 130.0, 128.9, 109.9, 52.4, 52.1, 49.9, 42.9, 28.2,
32.1, 32.0, 28.4, 28.3, 28.2, 28.1 ppm. IR (KBr): ν = 3083, 2991,
˜
2821, 1742, 1710, 1596, 1494, 1414, 1317, 1277, 1238, 1202, 1135,
1104, 1014, 856, 824, 777 cm–1. MS: m/z (%) = 519.32 (100) [M –
1]+, 521.28 (38) [M – 1]+. C28H25ClN2O6 (520.97): calcd. C 64.55,
H 4.84, N 5.38; found C 64.29, H 5.10, N 5.23.
21.1 ppm. IR (KBr): ν = 3105, 2989, 1742, 1707, 1599, 1493, 1419,
˜
1313, 1271, 1207, 1153, 1111, 1083, 1045, 1015, 857, 820 cm–1. MS:
m/z (%) = 533.29 (100) [M – 1]+, 535.31 (35) [M – 1]+.
C29H27ClN2O6 (535.00): calcd. C 65.11, H 5.09, N 5.24; found C
64.83, H 5.46, N 5.47.
1d: Yellow solid, yield: 52%, m.p. 270–272 °C. 1H NMR (600 MHz,
CDCl3): δ = 7.35 (s, 1 H, ArH), 7.21 (d, J = 8.4 Hz, 1 H, ArH),
7.07 (d, J = 7.8 Hz, 1 H, ArH), 6.87 (d, J = 8.4 Hz, 1 H, ArH),
6.56–6.52 (m, 2 H, ArH), 6.13–6.12 (m, 1 H, ArH), 3.93 (s, 3 H,
OCH3), 3.78 (s, 3 H, OCH3), 3.56 (s, 3 H, OCH3), 2.39–2.32 (m, 5
H, CH3, CH2), 2.04 (d, J = 17.4 Hz, 1 H, CH), 1.90 (d, J = 17.4 Hz,
1 H, CH), 0.97 (s, 6 H, CH3) ppm. 13C NMR (150 MHz, CDCl3):
δ = 164.1, 159.8, 137.5, 133.1, 131.3, 131.2, 130.1, 114.3, 114.0,
1i: Yellow solid, yield: 55%, m.p. 248–250 °C. 1H NMR (600 MHz,
CDCl3): δ = 7.59 (s, 1 H, NH), 7.50 (s, 3 H, ArH), 7.23–7.22 (m,
1 H, ArH), 7.18 (d, J = 8.4 Hz, 1 H, ArH), 6.86 (d, J = 8.4 Hz, 1
H, ArH), 6.57 (d, J = 8.4 Hz, 2 H, ArH), 6.19 (d, J = 7.8 Hz, 1 H,
109.9, 70.8, 55.4, 52.3, 51.9, 49.9, 42.7, 28.3, 28.1, 21.1 ppm. IR ArH), 3.91 (s, 3 H, OCH3), 3.77 (s, 3 H, OCH3), 3.54 (s, 3 H,
(KBr): ν = 2990, 1747, 1607, 1498, 1427, 1246, 1208, 1154, 1117, OCH3), 2.27 (s, 2 H, CH2), 2.00 (d, J = 17.1 Hz, 1 H, CH), 1.90
˜
1016, 864, 825 cm–1. MS: m/z (%) = 529.36 (100) [M – 1]+. (d, J = 17.5 Hz, 1 H, CH), 0.96 (s, 6 H, CH3) ppm. 13C NMR
Eur. J. Org. Chem. 2012, 1976–1983
© 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
www.eurjoc.org
1979

J. Sun, Y. Sun, H. Gao, C.-G. Yan
(150 MHz, CDCl3): δ = 164.0, 160.0, 138.5, 132.8, 130.9, 129.8, (549.02): calcd. C 65.63, H 5.32, N 5.10; found C 65.44, H 5.50, N
FULL PAPER
128.6, 114.6, 114.1, 111.1, 55.4, 52.4, 52.2, 49.8, 42.7, 32.0, 28.3,
4.87.
28.2 ppm. IR (KBr): ν = 2949, 1741, 1714, 1604, 1493, 1430, 1377,
˜
1n: Yellow solid, yield: 61%, m.p. 225–227 °C. 1H NMR (600 MHz,
CDCl3): δ = 7.59 (br. s, 1 H, ArH), 7.20–7.14 (m, 6 H, ArH), 7.07
(t, J = 7.8 Hz, 1 H, ArH), 6.84 (d, J = 7.8 Hz, 1 H, ArH), 6.71 (d,
J = 7.2 Hz, 2 H, ArH), 6.42 (d, J = 6.6 Hz, 1 H, ArH), 6.09–6.08
(m, 1 H, ArH), 4.79 (d, J = 16.2 Hz, 1 H, CH), 4.30 (d, J = 16.2 Hz,
1 H, CH), 3.92 (s, 3 H, OCH3), 3.51 (s, 3 H, OCH3), 2.36 (s, 3 H,
CH3), 2.26 (s, 2 H, CH2), 1.98 (d, J = 17.4 Hz, 1 H, CH), 1.83 (d,
J = 17.4 Hz, 1 H, CH), 0.96 (s, 3 H, CH3), 0.95 (s, 3 H, CH3) ppm.
13C NMR (150 MHz, CDCl3): δ = 163.9, 142.1, 139.7, 135.2, 130.8,
130.5, 129.5, 128.4, 127.3, 127.2, 123.6, 109.4, 52.3, 52.0, 49.9, 44.5,
1344, 1292, 1256, 1214, 1177, 1136, 1021, 958, 883, 826, 784 cm–1.
MS: m/z (%) = 549.32 (100) [M – 1]+, 551.30 (38) [M – 1]+.
C29H27ClN2O7 (550.99): calcd. C 63.22, H 4.94, N 5.08; found C
62.92, H 5.43, N 4.86.
1j: Yellow solid, yield: 40%, m.p. 252–254 °C. 1H NMR (600 MHz,
CDCl3): δ = 7.86 (s, 1 H, NH), 7.52 (br. s, 1 H, ArH), 7.40 (t, J =
7.2 Hz, 1 H, ArH), 7.35 (t, J = 7.2 Hz, 1 H, ArH), 7.28 (s, 1 H,
ArH), 7.23–7.22 (m, 1 H, ArH), 7.11 (t, J = 7.2 Hz, 1 H, ArH),
6.56 (br. s, 1 H, ArH), 6.31–6.30 (m, 1 H, ArH), 3.92 (s, 3 H,
OCH3), 3.55 (s, 3 H, OCH3), 2.28 (s, 2 H, CH2), 1.99 (d, J =
17.4 Hz, 1 H, CH), 1.89 (d, J = 17.4 Hz, 1 H, CH), 0.96 (s, 6 H,
CH3) ppm. 13C NMR (150 MHz, CDCl3): δ = 175.6, 164.0, 137.3,
132.6, 130.1, 130.0, 129.7, 128.9, 128.7, 111.2, 52.5, 52.2, 49.8, 42.8,
42.7, 28.1, 21.3 ppm. IR (KBr): ν = 2953, 1729, 1642, 1605, 1498,
˜
1429, 1366, 1306, 1251, 1192, 1117, 1026, 826 cm–1. MS: m/z (%)
= 589.56 (100) [M – 1]+. C36H34N2O6 (590.67): calcd. C 73.20, H
5.80, N 4.74; found C 72.86, H 6.23, N 4.49.
32.0, 28.2, 28.1, 20.7 ppm. IR (KBr): ν = 2954, 1746, 1597, 1485,
˜
1o: Yellow solid, yield: 67%, m.p. 246–249 °C. 1H NMR (600 MHz,
CDCl3): δ = 7.39–7.38 (m, 1 H, ArH), 7.25–7.23 (m, 1 H, ArH),
7.20–7.17 (m, 1 H, ArH), 7.16–7.13 (m, 2 H, ArH), 6.99 (d, J =
7.8 Hz, 1 H, ArH), 6.86 (d, J = 7.2 Hz, 1 H, ArH), 6.67 (d, J =
7.2 Hz, 2 H, ArH), 6.54–6.52 (m, 1 H, ArH), 6.33 (d, J = 7.2 Hz,
1430, 1343, 1278, 1215, 1136, 1019, 885, 830, 784, 757 cm–1. MS:
m/z (%) = 519.30 (100) [M – 1]+, 521.28 (18) [M – 1]+.
C28H25ClN2O6 (520.97): calcd. C 64.55, H 4.84, N 5.38; found C
64.22, H 5.10, N 5.24.
1k: Yellow solid, yield: 50%, m.p.230–233 °C. 1H NMR (600 MHz, 1 H, ArH), 6.11–6.10 (m, 1 H, ArH), 4.81 (d, J = 16.2 Hz, 1 H,
CDCl3): δ = 7.57 (d, J = 7.2 Hz, 1 H, NH), 7.32 (s, 1 H, ArH),
7.24 (br. s, 1 H, ArH), 7.16 (s, 2 H, ArH), 7.08–7.07 (m, 1 H, ArH),
6.83 (d, J = 7.8 Hz, 1 H, ArH), 6.60 (br. s, 1 H, ArH), 6.10 (d, J
= 7.8 Hz, 1 H, ArH), 4.36 (br. s, 2 H, CH2), 4.01–3.95 (m, 2 H,
CH), 4.27 (d, J = 16.2 Hz, 1 H, CH), 3.93 (s, 3 H, OCH3), 3.79 (s,
3 H, OCH3), 3.52 (s, 3 H, OCH3), 2.31 (s, 3 H, CH3), 2.28 (s, 2 H,
CH2), 1.99 (d, J = 17.4 Hz, 1 H, CH), 1.86 (d, J = 17.4 Hz, 1 H,
CH), 0.97 (s, 3 H, CH3), 0.96 (s, 3 H, CH3) ppm. 13C NMR
CH2), 2.30 (s, 3 H, CH3), 2.25 (br. s, 2 H, CH2), 1.99 (d, J = (150 MHz, CDCl3): δ = 164.0, 160.0, 139.8, 135.2, 133.3, 131.5,
17.4 Hz, 1 H, CH), 1.86 (d, J = 17.4 Hz, 1 H, CH), 1.37 (br. s, 3
131.3, 130.4, 128.3, 127.3, 127.1, 114.4, 109.2, 55.4, 52.3, 52.1, 49.9,
H, CH3), 1.08 (br. s, 3 H, CH3), 0.95 (s, 6 H, CH3) ppm. 13C NMR
44.4, 42.7, 28.2, 21.1 ppm. IR (KBr): ν = 2952, 1734, 1606, 1494,
˜
(150 MHz, CDCl3): δ = 163.7, 139.5, 135.0, 130.7, 130.3, 129.3, 1434, 1367, 1300, 1233, 1186, 1136, 1024, 979, 943, 873, 824,
123.4, 109.8, 61.3, 61.1, 50.0, 42.8, 28.8, 28.2, 21.2, 13.9 ppm. IR 763 cm–1. MS: m/z (%) = 619.42 (100) [M – 1]+. C37H36N2O7
(KBr): ν = 3165, 2942, 1735, 1605, 1491, 1424, 1261, 1200, 1128, (620.70): calcd. C 71.60, H 5.85, N 4.51; found C 71.42, H 6.15, N
˜
1029, 934, 866, 824, 765 cm–1. MS: m/z (%) = 527.42 (100) [M –
1]+. C31H32N2O6 (528.60): calcd. C 70.44, H 6.10, N 5.30; found C
70.25, H 6.52, N 5.01.
4.48.
1p: Yellow solid, yield: 65%, m.p. 274–275 °C. 1H NMR (600 MHz,
CDCl3): δ = 7.52 (br. s, 1 H, ArH), 7.29 (br. s, 1 H, ArH), 7.19 (d,
J = 7.8 Hz, 1 H, ArH), 7.14–7.13 (m, 1 H, ArH), 6.86 (d, J =
7.2 Hz, 1 H, ArH), 6.52–6.51 (m, 1 H, ArH), 6.10 (d, J = 7.2 Hz,
1 H, ArH), 3.93 (s, 3 H, OCH3), 3.54 (s, 3 H, OCH3), 3.47–3.42
(m, 1 H, CH), 3.08 (br. s, 1 H, CH), 2.31 (s, 3 H, CH3), 2.28 (br.
1l: Yellow solid, yield: 60%, m.p. 268–270 °C. 1H NMR (600 MHz,
CDCl3): δ = 7.54 (br. s, 1 H, NH), 7.23 (d, J = 6.6 Hz, 1 H, ArH),
7.19 (d, J = 8.4 Hz, 1 H, ArH), 7.13 (br. s, 1 H, ArH), 6.87 (d, J
= 7.8 Hz, 1 H, ArH), 6.58–6.55 (m, 2 H, ArH), 6.19 (d, J = 7.2 Hz,
1 H, ArH), 4.41–4.35 (m, 2 H, CH2), 4.05–3.99 (m, 2 H, CH2), s, 2 H, CH2), 1.99 (d, J = 17.4 Hz, 1 H, CH), 1.87 (d, J = 17.4 Hz,
3.78 (s, 3 H, OCH3), 2.27 (s, 2 H, CH2), 1.99 (d, J = 17.4 Hz, 1 H, 1 H, CH), 1.04 (br. s, 3 H, CH, CH2), 0.97 (s, 3 H, CH3), 0.96 (s, 3
CH), 1.90 (d, J = 17.4 Hz, 1 H, CH), 1.38 (br. s, 3 H, CH3), 1.14– H, CH3), 0.80 (t, J = 7.2 Hz, 3 H, CH3) ppm. 13C NMR (150 MHz,
1.12 (m, 3 H, CH3), 0.97 (s, 6 H, CH3) ppm. 13C NMR (150 MHz,
CDCl3): δ = 190.4, 189.4, 163.8, 163.7, 141.0, 139.9, 134.8, 132.4,
CDCl3): δ = 163.7, 159.9, 130.8, 130.0, 114.6, 114.1, 110.9, 61.5,
130.8, 130.3, 130.1, 130.0, 129.3, 128.4, 109.3, 52.4, 52.1, 49.9, 42.7,
61.3, 55.4, 50.0, 42.8, 28.4, 13.9 ppm. IR (KBr): ν = 3107, 2965,
40.1, 32.0, 31.9, 28.9, 28.2, 21.1, 20.1, 13.8 ppm. IR (KBr): ν =
˜
˜
1739, 1703, 1605, 1495, 1423, 1372, 1291, 1256, 1198, 1132, 1025,
2952, 1738, 1689, 1642, 1600, 1487, 1428, 1295, 1227, 1189, 1136,
875, 825, 780 cm–1. MS: m/z (%) = 577.58 (100) [M – 1]+. 1012, 879, 820 cm–1. MS: m/z (%) = 613.92 (100) [M + Na]+.
C31H31ClN2O7 (579.05): calcd. C 64.30, H 5.40, N 4.84; found C C33H35ClN2O6 (591.10): calcd. C 67.05, H 5.97, N 4.74; found C
64.57, H 5.62, N 4.59.
66.71, H 6.16, N 4.66.
1m: Yellow solid, yield: 55%, m.p. 292–293 °C. 1H NMR
(600 MHz, CDCl3): δ = 7.60 (br. s, 1 H, NH), 7.56 (d, J = 7.2 Hz,
1q: Yellow solid, yield: 70%, m.p. 250–251 °C. 1H NMR (600 MHz,
CDCl3): δ = 7.37 (d, J = 7.2 Hz, 2 H, ArH), 7.24 (d, J = 8.4 Hz, 1
1 H, ArH), 7.37–7.36 (m, 1 H, ArH), 7.26–7.24 (m, 2 H, ArH), H, ArH), 7.12 (d, J = 7.8 Hz, 1 H, ArH), 7.03–7.02 (m, 1 H, ArH),
7.08 (t, J = 7.2 Hz, 1 H, ArH), 7.04–7.03 (m, 1 H, ArH), 6.64–6.63
(m, 1 H, ArH), 6.18 (d, J = 7.8 Hz, 1 H, ArH), 4.36 (br. s, 2 H,
6.50 (d, J = 7.8 Hz, 1 H, ArH), 6.10 (d, J = 8.4 Hz, 1 H, ArH),
3.92 (s, 3 H, OCH3), 3.52 (s, 3 H, OCH3), 3.43–3.42 (m, 1 H, CH),
CH2), 4.01–3.95 (m, 2 H, CH2), 2.26 (s, 2 H, CH2), 1.98 (d, J = 3.09 (br. s, 1 H, CH), 2.34 (s, 3 H, CH3), 2.28 (br. s, 2 H, CH2),
17.4 Hz, 1 H, CH), 1.84 (d, J = 17.4 Hz, 1 H, CH), 1.37 (br. s, 3
H, CH3), 1.09–1.07 (m, 3 H, CH3), 0.96 (s, 6 H, CH3) ppm. 13C
NMR (150 MHz, CDCl3): δ = 167.6, 163.6, 139.7, 136.1, 135.6,
131.0, 130.0, 128.9, 123.6, 110.1, 61.4, 61.2, 49.9, 42.9, 28.2, 28.1,
1.97 (d, J = 17.4 Hz, 1 H, CH), 1.83 (d, J = 17.4 Hz, 1 H, CH),
1.12–1.05 (m, 4 H, CH2), 0.97 (s, 3 H, CH3), 0.96 (s, 3 H, CH3),
0.84 (t, J = 7.2 Hz, 3 H, CH3) ppm. 13C NMR (150 MHz, CDCl3):
δ = 163.7, 139.8, 136.1, 135.7, 133.2, 132.0, 131.5, 130.6, 129.8,
128.8, 108.3, 70.2, 52.4, 52.0, 49.9, 42.8, 40.0, 32.1, 29.1, 28.3, 28.2,
13.9 ppm. IR (KBr): ν = 3081, 2987, 2881, 2814, 1740, 1703, 1598,
˜
1492, 1413, 1309, 1274, 1239, 1199, 1136, 1097, 1023, 919, 859,
21.1, 20.1, 13.8 ppm. IR (KBr): ν = 2949, 1736, 1697, 1637, 1599,
˜
826 cm–1. MS: m/z (%) = 547.37 (100) [M – 1]+. C30H29ClN2O6
1493, 1425, 1360, 1295, 1187, 1105, 1011, 817 cm–1. MS: m/z (%)
1980
www.eurjoc.org
© 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Eur. J. Org. Chem. 2012, 1976–1983

Synthesis of Spiro[indoline-3,2Ј-quinoline] through a 4CR
= 613.90 (100) [M + Na]+. C33H35ClN2O6 (591.10): calcd. C 67.05, C33H27ClN2O6 (583.04): calcd. C 67.98, H 4.67, N 4.80; found C
H 5.97, N 4.74; found C 67.34, H 6.19, N 4.46.
67.70, H 4.76, N 4.43.
2a: Yellow solid, yield: 72%, m.p. 236–238 °C. 1H NMR (600 MHz,
CDCl3): δ = 7.41 (br. s, 1 H, ArH), 7.27 (br. s, 1 H, ArH), 7.19–
7.17 (m, 1 H, ArH), 7.14 (t, J = 7.2 Hz, 2 H, ArH), 6.99 (d, J =
7.8 Hz, 1 H, ArH), 6.84–6.83 (m, 1 H, ArH), 6.66 (d, J = 7.2 Hz,
2 H, ArH), 6.54–6.52 (m, 1 H, ArH), 6.31 (d, J = 7.8 Hz, 1 H,
ArH), 6.15 (d, J = 7.8 Hz, 1 H, ArH), 4.82 (d, J = 16.2 Hz, 1 H,
2e: Yellow solid, yield: 67%, m.p. 222–225 °C. 1H NMR (600 MHz,
CDCl3): δ = 7.38 (s, 1 H, ArH), 7.23–7.22 (m, 1 H, ArH), 7.10 (d,
J = 7.8 Hz, 1 H, ArH), 6.86–6.84 (m, 1 H, ArH), 6.52–7.50 (m, 1
H, ArH), 6.47 (d, J = 7.8 Hz, 1 H, ArH), 6.10–6.08 (m, 1 H, ArH),
3.92 (s, 3 H, OCH3), 3.74 (s, 3 H, OCH3), 3.51 (s, 3 H, OCH3),
3.44–3.41 (m, 1 H, CH), 3.11–3.08 (m, 1 H, CH), 2.38 (br. s, 2 H,
CH), 4.28 (d, J = 16.2 Hz, 1 H, CH), 3.92 (s, 3 H, OCH3), 3.77 (s, CH2), 2.35 (s, 3 H, CH3), 2.15–2.11 (m, 1 H, CH), 2.03–1.98 (m, 1
3 H, OCH3), 3.51 (s, 3 H, OCH3), 2.40 (br. s, 2 H, CH2), 2.32 (s, H, CH), 1.87–1.82 (m, 2 H, CH2), 1.07–1.05 (m, 3 H, CH, CH2),
3 H, CH3), 2.15–2.11 (m, 1 H, CH), 2.04–1.99 (m, 1 H, CH), 1.86–
0.96 (br. s, 1 H, CH), 0.80 (t, J = 7.2 Hz, 3 H, CH3) ppm. 13C
1.84 (m, 2 H, CH2) ppm. 13C NMR (150 MHz, CDCl3): δ = 190.9, NMR (150 MHz, CDCl3): δ = 190.9, 190.8, 173.6, 163.9, 159.9,
174.2, 168.5, 163.9, 160.0, 139.7, 135.2, 133.2, 131.4, 131.3, 130.7,
130.3, 130.2, 128.4, 127.3, 127.0, 125.2, 114.4, 114.2, 109.1, 70.5,
139.9, 132.8, 131.4, 131.2, 130.1, 114.1, 113.7, 108.1, 70.2, 55.4,
52.2, 51.8, 39.9, 36.2, 29.5, 29.2, 21.0, 20.4, 20.1, 13.7 ppm. IR
55.4, 52.3, 44.3, 36.3, 29.5, 21.1, 20.4 ppm. IR (KBr): ν = 2949,
(KBr): ν = 2947, 1718, 1600, 1488, 1429, 1368, 1336, 1293, 1248,
˜
˜
1731, 1606, 1498, 1422, 1366, 1335, 1293, 1247, 1189, 1115, 1026,
994, 948, 844, 759 cm–1. MS: m/z (%) = 615.78 (100) [M + Na]+.
C35H32N2O7 (592.65): calcd. C 70.93, H 5.44, N 4.73; found C
70.68, H 5.70, N 4.65.
1192, 1019, 844, 798, 750 cm–1. MS: m/z (%) = 581.88 (100) [M +
Na]+. C32H34N2O7 (558.63): calcd. C 68.80, H 6.13, N 5.01; found
C 68.53, H 6.45, N 4.79.
2f: Yellow solid, yield: 61%, m.p. 215–218 °C. 1H NMR (600 MHz,
CDCl3): δ = 7.39 (s, 1 H, ArH), 7.19 (d, J = 7.8 Hz, 1 H, ArH),
7.16 (d, J = 7.8 Hz, 1 H, ArH), 7.09 (d, J = 7.8 Hz, 1 H, ArH),
2b: Yellow solid, yield: 62%, m.p. 259–260 °C. 1H NMR (600 MHz,
CDCl3): δ = 7.62 (d, J = 7.2 Hz, 1 H, ArH), 7.24–7.14 (m, 6 H,
ArH), 7.07 (t, J = 7.8 Hz, 1 H, ArH), 6.84 (d, J = 8.4 Hz, 1 H, 6.81 (d, J = 7.8 Hz, 1 H, ArH), 6.46 (d, J = 7.8 Hz, 1 H, ArH),
ArH), 6.71 (d, J = 7.2 Hz, 2 H, ArH), 6.41 (d, J = 7.8 Hz, 1 H,
ArH), 6.13 (d, J = 7.8 Hz, 1 H, ArH), 4.79 (d, J = 16.2 Hz, 1 H,
6.06 (d, J = 7.8 Hz, 1 H, ArH), 3.92 (s, 3 H, OCH3), 3.51 (s, 3 H,
OCH3), 3.45–3.40 (m, 1 H, CH), 3.09–3.04 (m, 1 H, CH), 2.39 (br.
CH), 4.32 (d, J = 16.2 Hz, 1 H, CH), 3.92 (s, 3 H, OCH3), 3.51 (s, s, 2 H, CH2), 2.35 (s, 3 H, CH3), 2.28 (s, 3 H, CH3), 2.15–2.11 (m,
3 H, OCH3), 2.40 (br. s, 2 H, CH2), 2.34 (s, 3 H, CH3), 2.13–2.08 1 H, CH), 2.02–1.98 (m, 1 H, CH), 1.85–1.81 (m, 2 H, CH2), 1.04–
(m, 1 H, CH), 2.01–1.96 (m, 1 H, CH), 1.88–1.81 (m, 2 H,
CH2) ppm. 13C NMR (150 MHz, CDCl3): δ = 190.9, 174.3, 163.9,
142.1, 139.6, 135.1, 135.0, 130.8, 130.4, 129.9, 129.4, 129.3, 128.4,
127.3, 127.1, 123.5, 109.4, 70.2, 60.4, 52.4, 52.1, 44.4, 36.3, 29.6,
1.00 (m, 3 H, CH, CH2), 0.89–0.88 (m, 1 H, CH), 0.79 (t, J =
6.6 Hz, 3 H, CH3) ppm. 13C NMR (150 MHz, CDCl3): δ = 190.9,
190.8, 173.5, 163.8, 139.9, 139.5, 134.9, 132.8, 131.2, 130.0, 129.0,
128.8, 108.0, 70.1, 52.3, 51.9, 39.9, 36.3, 29.5, 29.0, 21.1, 20.4, 20.1,
21.3, 21.0, 20.4, 14.2 ppm. IR (KBr): ν = 2950, 1730, 1645, 1609,
13.8 ppm. IR (KBr): ν = 2951, 1735, 1689, 1636, 1601, 1494, 1426,
˜
˜
1500, 1413, 1368, 1265, 1231, 1188, 1140, 1003, 937, 751 cm–1. MS:
m/z (%) = 585.63 (100) [M + Na]+. C34H30N2O6 (562.62): calcd. C
72.58, H 5.37, N 4.98; found C 72.33, H 5.62, N 4.67.
1365, 1297, 1236, 1191, 1147, 1027, 980, 815 cm–1. MS: m/z (%) =
565.92 (100) [M + Na]+. C32H34N2O6 (542.63): calcd. C 70.83, H
6.32, N 5.16; found C 70.72, H 6.56, N 4.85.
2c: Yellow solid, yield: 53%, m.p. 254–255 °C. 1H NMR (600 MHz,
CDCl3): δ = 7.42 (br. s, 1 H, ArH), 7.37 (br. s, 3 H, ArH), 7.19–
7.13 (m, 1 H, ArH), 7.15–7.13 (m, 2 H, ArH), 7.07–7.04 (m, 1 H,
ArH), 6.98 (d, J = 7.8 Hz, 1 H, ArH), 6.67 (d, J = 7.8 Hz, 2 H,
2g: Yellow solid, yield: 70%, m.p. 234–235 °C. 1H NMR (600 MHz,
CDCl3): δ = 7.34 (br. s, 1 H, ArH), 7.23 (d, J = 8.4 Hz, 1 H, ArH),
7.01 (t, J = 7.8 Hz, 1 H, ArH), 6.86 (d, J = 6.6 Hz, 1 H, ArH),
6.54–6.51 (m, 2 H, ArH), 6.16 (d, J = 7.2 Hz, 1 H, ArH), 3.92 (s,
ArH), 6.29–6.26 (m, 2 H, ArH), 4.66 (d, J = 16.2 Hz, 1 H, CH), 3 H, OCH3), 3.75 (s, 3 H, OCH3), 3.53 (s, 3 H, OCH3), 3.46–3.42
4.32 (d, J = 16.2 Hz, 1 H, CH), 3.93 (s, 3 H, OCH3), 3.50 (s, 3 H, (m, 1 H, CH), 3.13 (br. s, 1 H, CH), 2.39 (br. s, 2 H, CH2), 2.15–
OCH3), 2.41 (br. s, 2 H, CH2), 2.33 (s, 3 H, CH3), 2.14–2.10 (m, 1
2.12 (m, 1 H, CH), 2.03–2.00 (m, 1 H, CH), 1.86 (m, 2 H, CH2),
H, CH), 2.02–1.99 (m, 1 H, CH), 1.86–1.83 (m, 2 H, CH2) ppm. 1.08–1.04 (m, 3 H, CH, CH2), 1.00–0.99 (m, 1 H, CH), 0.81 (t, J
13C NMR (150 MHz, CDCl3): δ = 174.1, 163.9, 139.7, 137.7, 135.2, = 7.2 Hz, 3 H, CH3) ppm. 13C NMR (150 MHz, CDCl3): δ = 190.9,
133.3, 131.3, 130.3, 129.8, 129.5, 128.8, 128.5, 127.3, 127.0, 109.2,
109.2, 70.4, 52.4, 52.1, 44.4, 36.3, 29.6, 21.1, 20.5 ppm. IR (KBr):
190.8, 173.6, 163.8, 160.1, 158.5, 138.5, 131.4, 130.0, 117.3, 117.2,
114.3, 113.9, 109.0, 108.9, 70.2, 55.4, 52.4, 52.0, 40.1, 36.3, 29.5,
ν = 2949, 1738, 1701, 1640, 1603, 1494, 1423, 1365, 1297, 1237,
29.1, 20.4, 20.1, 13.7 ppm. IR (KBr): ν = 2956, 1737, 1687, 1633,
˜
˜
1187, 1111, 993, 818, 756 cm–1. MS: m/z (%) = 585.75 (100) [M +
Na]+. C34H30N2O6 (562.62): calcd. C 72.58, H 5.37, N 4.98; found
C 72.20, H 5.77, N 4.82.
1600, 1491, 1433, 1363, 1299, 1249, 1187, 1144, 1031, 991, 857,
819 cm–1. MS: m/z (%) = 585.83 (100) [M + Na]+. C31H31FN2O7
(562.59): calcd. C 66.18, H 5.55, N 4.98; found C 65.80, H 5.79, N
4.86.
2d: Yellow solid, yield: 60%, m.p. 244–247 °C. 1H NMR (600 MHz,
CDCl3): δ = 7.61 (d, J = 7.2 Hz, 1 H, ArH), 7.30 (s, 2 H, ArH),
2h: Yellow solid, yield: 64%, m.p. 252–253 °C. 1H NMR (600 MHz,
7.24–7.21 (m, 4 H, ArH), 7.08 (t, J = 7.8 Hz, 1 H, ArH), 7.01–6.99 CDCl3): δ = 7.54 (br. s, 1 H, ArH), 7.28 (br. s, 1 H, ArH), 7.17 (br.
(m, 1 H, ArH), 6.72–6.71 (m, 2 H, ArH), 6.48 (d, J = 7.8 Hz, 1 H,
ArH), 6.18 (d, J = 8.4 Hz, 1 H, ArH), 4.84 (d, J = 16.2 Hz, 1 H,
s, 2 H, ArH), 6.85 (d, J = 7.8 Hz, 1 H, ArH), 6.50 (d, J = 8.4 Hz,
1 H, ArH), 6.13 (d, J = 8.4 Hz, 1 H, ArH), 3.93 (s, 3 H, OCH3),
CH), 4.32 (d, J = 16.2 Hz, 1 H, CH), 3.92 (s, 3 H, OCH3), 3.51 (s, 3.53 (s, 3 H, OCH3), 3.46–3.43 (m, 1 H, CH), 3.08 (br. s, 1 H, CH),
3 H, OCH3), 2.41–2.36 (m, 2 H, CH2), 2.10–2.07 (m, 1 H, CH), 2.40 (br. s, 2 H, CH2), 2.29 (s, 3 H, CH3), 2.15–2.09 (m, 1 H, CH),
2.00–1.95 (m, 1 H, CH), 1.89–1.85 (m, 2 H, CH2) ppm. 13C NMR 2.03–1.99 (m, 1 H, CH), 1.86–1.85 (m, 2 H, CH2), 1.04–1.03 (m, 3
(150 MHz, CDCl3): δ = 190.9, 174.1, 168.2, 142.0, 136.1, 135.7, H, CH, CH2), 0.90 (br. s, 1 H, CH), 0.80 (t, J = 7.2 Hz, 3 H,
134.9, 131.8, 130.1, 129.1, 128.6, 127.6, 127.1, 123.7, 109.5, 70.2,
CH3) ppm. 13C NMR (150 MHz, CDCl3): δ = 190.9, 190.8, 173.4,
168.2, 163.7, 141.0, 139.9, 134.7, 130.8, 130.2, 130.0, 129.2, 128.7,
128.3, 109.3, 69.9, 52.3, 52.1, 40.1, 36.2, 29.5, 28.9, 21.1, 20.4, 20.1,
58.3, 52.4, 52.1, 44.5, 36.2, 29.6, 20.4 ppm. IR (KBr): ν = 2950,
˜
1735, 1640, 1604, 1495, 1412, 1367, 1285, 1226, 1180, 1139, 1004,
935, 863 cm–1. MS: m/z (%)
=
605.96 (100) [M
+
Na]+.
13.8 ppm. IR (KBr): ν = 2956, 2871, 1737, 1686, 1638, 1602, 1489,
˜
Eur. J. Org. Chem. 2012, 1976–1983
© 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
www.eurjoc.org
1981

J. Sun, Y. Sun, H. Gao, C.-G. Yan
FULL PAPER
1427, 1365, 1299, 1227, 1188, 1141, 1028, 989, 937, 894, 821,
789 cm–1. MS: m/z (%) = 585.93 (100) [M + Na]+. C31H31ClN2O6
(563.05): calcd. C 66.13, H 5.55, N 4.98; found C 66.37, H 5.94, N
4.70.
0.92 (t, J = 7.2 Hz, 3 H, CH3) ppm. 13C NMR (150 MHz, CDCl3):
δ = 189.8, 175.2, 166.9, 163.0, 138.8, 134.8, 131.3, 131.0, 130.9,
129.7, 129.4, 129.1, 128.9, 125.0, 109.4, 70.1, 60.3, 60.2, 35.8, 29.0,
20.6, 20.5, 20.0, 13.7, 13.1 ppm. IR (KBr): ν = 2947, 1733, 1604,
˜
1492, 1427, 1311, 1275, 1199, 1115, 1022, 971, 823 cm–1. MS: m/z
(%) = 537.88 (100) [M + Na]+. C30H30N2O6 (514.58): calcd. C
70.02, H 5.88, N 5.44; found C 69.67, H 6.21, N 5.19.
2i: Yellow solid, yield: 59%, m.p. 241–244 °C. 1H NMR (600 MHz,
CDCl3): δ = 7.38–7.35 (m, 2 H, ArH), 7.29 (d, J = 8.4 Hz, 1 H,
ArH), 7.12 (d, J = 7.8 Hz, 1 H, ArH), 7.02–7.00 (m, 1 H, ArH),
6.49 (d, J = 7.8 Hz, 1 H, ArH), 6.15–6.13 (m, 1 H, ArH), 3.92 (s,
3 H, OCH3), 3.52 (s, 3 H, OCH3), 3.45–3.41 (m, 1 H, CH), 3.11–
3.09 (m, 1 H, CH), 2.40 (br. s, 2 H, CH2), 2.35 (s, 3 H, CH3), 2.13–
2.09 (m, 1 H, CH), 2.01–1.97 (m, 1 H, CH), 1.88–1.86 (m, 2 H,
CH2), 1.08–1.05 (m, 3 H, CH, CH2), 0.94 (br. s, 1 H, CH), 0.84 (t,
J = 7.2 Hz, 3 H, CH3) ppm. 13C NMR (150 MHz, CDCl3): δ =
190.9, 173.4, 168.3, 163.7, 163.6, 163.5, 139.8, 136.0, 135.6, 133.1,
131.9, 131.5, 130.5, 129.7, 128.7, 125.3, 125.2, 108.3, 70.1, 52.4,
CCDC-842844 (for 1e), -842847 (for 1j), -850310 (for 2e), and
-850311 (for 2k) contain the supplementary crystallographic data
for this paper. These data can be obtained free of charge from The
Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/
data_request/cif.
Supporting Information (see footnote on the first page of this arti-
cle): Experimental details and spectroscopic data for all new com-
pounds.
52.0, 40.0, 36.2, 29.6, 29.1, 21.1, 20.4, 20.1, 13.8 ppm. IR (KBr): ν
˜
= 2946, 1733, 1698, 1643, 1603, 1494, 1422, 1365, 1296, 1236, 1191,
1100, 987, 815 cm–1. MS: m/z (%) = 585.97 (100) [M + Na]+.
C31H31ClN2O6 (563.05): calcd. C 66.13, H 5.55, N 4.98; found C
65.82, H 5.675, N 4.80.
Acknowledgments
This work was financially supported by the National Natural Sci-
ence Foundation of China (Grant No. 21172189) and the Priority
Academic Program Development of Jiangsu Higher Education In-
stitutions.
2j: Yellow solid, yield: 72%, m.p. 235–236 °C. 1H NMR (600 MHz,
CDCl3): δ = 8.18 (d, J = 7.2 Hz, 1 H, ArH), 7.70 (d, J = 6.6 Hz, 1
H, ArH), 7.60 (t, J = 7.8 Hz, 1 H, ArH), 7.45 (s, 1 H, ArH), 7.25
(br. s, 1 H, ArH), 7.15 (d, J = 7.2 Hz, 1 H, ArH), 7.10 (br. s, 1 H,
ArH), 3.93 (s, 3 H, OCH3), 3.53 (s, 3 H, OCH3), 3.38–3.36 (m, 1
H, CH), 3.14–3.12 (m, 1 H, CH), 2.43–2.42 (m, 2 H, CH2), 2.39 (s,
3 H, CH3), 2.12–2.09 (m, 1 H, CH), 2.03–1.90 (m, 3 H, CH2, CH),
1.07–0.95 (m, 4 H, CH2), 0.94 (br. s, 1 H, CH), 0.80–079 (m, 3 H,
CH3) ppm. 13C NMR (150 MHz, CDCl3): δ = 190.9, 173.2, 168.1,
163.5, 148.5, 14.7, 139.8, 139.4, 138.6, 138.4, 137.0, 135.7, 133.8,
133.3, 132.0, 131.7, 130.3, 130.0, 129.5, 125.9, 125.4, 125.3, 125.2,
124.7, 124.2, 108.5, 108.4, 70.2, 70.1, 52.4, 52.1, 40.0, 39.9, 36.2,
[1] a) R. J. Sundberg, The Chemistry of Indoles, Academic Press,
New York, 1996; b) A. H. Abdel-Rahman, E. M. Keshk, M. A.
Hanna, Sh. M. El-Bady, Bioorg. Med. Chem. 2004, 12, 2483–
2488.
[2] a) C. Marti, E. M. Carreia, Eur. J. Org. Chem. 2003, 2209; b)
A. Ashimori, B. Bachand, L. E. Overman, D. J. Poon, J. Am.
Chem. Soc. 1998, 120, 6477–6487; c) P. R. Sebahar, R. M. Wil-
liams, J. Am. Chem. Soc. 2000, 122, 5666–5667.
[3] J. Ma, S. M. Hecht, Chem. Commun. 2004, 1190–1192.
[4] a) S.-L. Zhu, S.-J. Jia, Y. Zhang, Tetrahedron 2007, 63, 9365–
9372; b) R. S. Kumar, S. Perumal, Tetrahedron Lett. 2007, 48,
7164–7168; c) R. Gr. Redkin, L. A. Shemchuk, V. P. Chernykh,
O. V. Shishkin, S. V. Shishkina, Tetrahedron 2007, 63, 11444–
11450.
29.8, 29.1, 29.0, 21.1, 20.5, 20.0, 19.9, 13.6 ppm. IR (KBr): ν =
˜
2950, 1728, 1644, 1607, 1499, 1418, 1350, 1292, 1189, 994, 901,
810 cm–1. MS: m/z (%) = 596.92 (100) [M + Na]+. C31H31N3O8
(573.60): calcd. C 64.91, H 5.45, N 7.33; found C 64.78, H 5.81, N
7.05.
[5] a) G. Shanthi, G. Subbulakshmi, P. T. Perumal, Tetrahedron
2007, 63, 2057–2063; b) A. A. Mohammadi, M. Dabiri, H. Qa-
raat, Tetrahedron 2009, 65, 3804–3808; c) A. H. Abdel-Rah-
man, E. M. Keshk, M. A. Hanna, Sh. M. El-Bady, Bioorg.
Med. Chem. 2004, 12, 2483–2488.
[6] a) D. Basavaiah, R. K. Reddy, Org. Lett. 2007, 9, 57–60; b)
R. R. Kumar, S. Perumal, P. Senthilkumar, P. Yogeeswari, D.
Sriram, Eur. J. Med. Chem. 2009, 44, 3821–3829; c) R. Muru-
gan, S. Anbazhagan, S. S. Narayanan, Eur. J. Med. Chem.
2009, 44, 3272–3279.
[7] a) H. Liu, D. L. Dou, D. Q. Shi, J. Comb. Chem. 2010, 12, 633–
637; b) H. Liu, G. L. Dou, D. Q. Shi, J. Comb. Chem. 2010,
12, 292–294; c) Y. L. Li, H. Chen, C. L. Shi, D. Q. Shi, S. J. Ji,
J. Comb. Chem. 2010, 12, 231–237.
2k: Yellow solid, yield: 51%, m.p. 242–243 °C. 1H NMR
(600 MHz, CDCl3): δ = 7.42 (s, 1 H, ArH), 7.29 (br. s, 2 H, ArH),
7.22 (br. s, 3 H, ArH), 7.01 (d, J = 7.8 Hz, 2 H, ArH), 6.69–6.68
(m, 2 H, ArH), 6.36 (d, J = 7.8 Hz, 1 H, ArH), 6.20 (d, J = 8.4 Hz,
1 H, ArH), 4.85 (d, J = 16.2 Hz, 1 H, CH), 4.38 (br. s, 2 H, CH2),
4.26 (d, J = 16.2 Hz, 1 H, CH), 4.07–4.04 (m, 1 H, CH), 3.94 (br.
s, 1 H, CH), 2.40–2.39 (m, 2 H, CH2), 2.33 (s, 3 H, CH3), 2.09–
2.05 (m, 1 H, CH), 1.99–1.97 (m, 1 H, CH), 1.87–1.85 (m, 2 H,
CH2), 1.39 (t, J = 7.2 Hz, 3 H, CH3), 1.08 (br. s, 3 H, CH3) ppm.
13C NMR (150 MHz, CDCl3): δ = 190.9, 190.8, 174.1, 167.7, 163.5,
139.7, 136.2, 135.6, 135.0, 133.4, 131.9, 131.4, 130.8, 130.0, 129.0,
128.5, 127.5, 127.1, 125.3, 109.2, 70.3, 61.4, 61.1, 44.5, 36.3, 29.8,
[8] a) P. Shanmugam, B. Viswambharan, S. Madhavan, Org. Lett.
2007, 9, 4095–4098; b) J. J. Badillo, G. E. Arevalo, J. C. Fet-
tinger, A. K. Franz, Org. Lett. 2011, 13, 418–421; c) N. V.
Lakshmi, P. Thirumurugan, P. T. Perumal, Tetrahedron Lett.
2010, 51, 1064–1068.
[9] a) P. Shanmugam, B. Viswambharan, S. Madhavan, Org. Lett.
2007, 9, 4095–4098; b) P. Shanmugam, B. Viswambharan, K.
Selvakumar, S. Madhavan, Tetrahedron Lett. 2008, 49, 2611–
2615.
[10] a) X. C. Zhang, S. H. Cao, Y. Wei, M. Shi, Org. Lett. 2011, 13,
1142–1145; b) H. P. Deng, Y. Wei, M. Shi, Org. Lett. 2011, 13,
3348–3351.
[11] a) L. Wang, Y. Zhang, H. Y. Hu, H. K. Fun, J. H. Xu, J. Org.
Chem. 2005, 70, 3850–3858; b) B. Viswambharan, K. Selvaku-
mar, S. Madhavan, P. Shanmugam, Org. Lett. 2010, 12, 2108–
21.1, 20.4, 18.4, 13.9, 13.7 ppm. IR (KBr): ν = 2969, 1731, 1644,
˜
1596, 1489, 1419, 1369, 1331, 1291, 1251, 1186, 1099, 1019,
801 cm–1. MS: m/z (%) = 647.99 (100) [M + Na]+. C36H33ClN2O6
(625.12): calcd. C 69.17, H 5.32, N 4.48; found C 68.82, H 5.77, N
4.23.
2l: Yellow solid, yield: 78%, m.p. Ͼ250 °C. 1H NMR (600 MHz,
CDCl3): δ = 10.11 (s, 1 H,NH), 7.30 (s, 1 H, ArH), 7.22 (d, J =
8.4 Hz, 1 H, ArH), 7.13–7.12 (m, 1 H, ArH), 7.04 (d, J = 7.8 Hz,
1 H, ArH), 6.92 (d, J = 7.8 Hz, 1 H, ArH), 6.46 (d, J = 7.8 Hz, 1
H, ArH), 6.24–6.22 (m, 1 H, ArH), 4.21–4.12 (m, 2 H, CH2), 3.82–
3.79 (m, 2 H, CH2), 2.35 (br. s, 1 H, CH), 2.29 (s, 3 H, CH3), 2.24–
2.18 (m, 5 H, CH2, CH3), 2.04–2.03 (m, 2 H, CH2), 1.76–1.73 (m,
1 H, CH), 1.72–1.68 (m, 1 H, CH), 1.25 (t, J = 7.2 Hz, 3 H, CH3),
1982
www.eurjoc.org
© 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Eur. J. Org. Chem. 2012, 1976–1983

Synthesis of Spiro[indoline-3,2Ј-quinoline] through a 4CR
2111; c) J. Q. Wang, E. A. Crane, K. A. Scheidt, Org. Lett.
2011, 13, 3086–3089.
Maleki, A. H. Rezayan, A. Sarvary, Mol. Diversity 2011, 15,
41–68.
[12] a) A. Bazgir, Z. Noroozi Tisseh, P. Mirzaei, Tetrahedron Lett.
2008, 49, 5165–5168; b) K. Jadidi, R. Ghahremanzadeh, A.
Bazgir, Tetrahedron 2009, 65, 2005–2009; c) M. Dabiri, S. C.
Azimi, H. R. Khavasi, A. Bazgir, Tetrahedron 2008, 64, 7307–
7311; d) K. Jadidi, R. Ghahremanzadeh, A. Bazgir, J. Comb.
Chem. 2009, 11, 341–344.
[13] a) S. J. Gao, C. H. Tsai, C. Tseng, C. F. Yao, Tetrahedron 2008,
64, 9143–9149; b) Y. M. Litvinov, V. Y. Mortikov, A. M. Shes-
topalov, J. Comb. Chem. 2008, 10, 741–745; c) B. Liang, S.
Kalidindi, J. A. Porco Jr., C. R. J. Stephenson, Org. Lett. 2010,
12, 572–575; d) W. B. Chen, Z. J. Wu, Q. L. Pei, N. F. Cun,
X. M. Zhang, W. C. Yuan, Org. Lett. 2010, 12, 3132–3135.
[14] a) J. Mokhtari, A. Alizadeh, Helv. Chim. Acta 2011, 94, 1315–
1319; b) M. Dabiri, Z. N. Tisseh, M. Nobahr, A. Bazgir, Helv.
Chim. Acta 2011, 94, 824–830; c) J. Quiroga, S. Portillo, A.
Pérez, J. Gálvez, R. Abonia, B. Insuasty, Tetrahedron Lett.
2011, 52, 2664–2666.
[15] a) R. Ghahremanzadeh, M. Sayyafi, S. Ahadi, A. Bazgir, J.
Comb. Chem. 2009, 11, 393–396; b) R. Ghahremanzadeh, S.
Ahadi, G. I. Shakibaei, A. Bazgir, Tetrahedron Lett. 2010, 51,
499–502; c) R. Ghahremanzadeh, G. I. Shakibaei, S. Ahadi, A.
Bazgir, J. Comb. Chem. 2010, 12, 191–194; d) G. I. Shakibaei,
A. Feiz, H. R. Khavasi, A. A. Soorki, A. Bazgir, ACS Comb.
Sci. 2011, 13, 96–99.
[16] a) M. S. Al-Thebebiti, Heterocycles 1998, 48, 145–150; b) V. V.
Kouznetsov, J. B. Ferero, D. F. A. Torres, Tetrahedron Lett.
2008, 49, 5855–5857.
[18]
[19]
a) J. S. Yadav, B. V. S. Reddy, N. N. Yadav, M. K. Gupta, B.
Sridhar, J. Org. Chem. 2008, 73, 6857–6859; b) Q. Zhu, H. F.
Jiang, J. Li, S. Liu, C. Xia, M. Zhang, J. Comb. Chem. 2009,
11, 685–696; c) I. Yavari, A. Mirzaei, L. Moradi, G. Khalili,
Tetrahedron Lett. 2010, 51, 396–398; d) A. Alizadeh, S. Ros-
tamnia, L. G. Zhu, Tetrahedron Lett. 2010, 51, 4750–4754.
a) A. A. Esmaili, A. Bodaghi, Tetrahedron 2003, 59, 1169–1171;
b) A. A. Esmaeili, M. Darbanian, Tetrahedron 2003, 59, 5545–
5548; c) V. Nair, A. U. Vinod, N. Abhilash, R. S. Menon, V.
Santhi, R. L. Varma, S. Viji, S. Mathewa, R. Srinivas, Tetrahe-
dron 2003, 59, 10279–10286; d) V. Nair, S. Devipriya, E. Suresh,
Tetrahedron 2008, 64, 3567–3577.
a) A. A. Esmaelli, M. Nazer, Synlett 2009, 2119–2122; b) A. A.
Esmaeili, H. Vesalipoor, R. Hosseinabadi, A. F. Zavareh, N. A.
Naseri, E. Ghiamati, Tetrahedron Lett. 2011, 52, 4865.
S. E. Kiruthika, N. V. Lakshmi, B. R. Banu, P. T. Perumal, Tet-
rahedron Lett. 2011, 52, 6508–6511.
[20]
[21]
[22] a) J. Sun, E. Y. Xia, Q. Wu, C. G. Yan, Org. Lett. 2010, 12,
3678–3681; b) J. Sun, E. Y. Xia, Q. Wu, C. G. Yan, ACS Comb.
Sci. 2011, 13, 421–426; c) J. Sun, Y. Sun, E. Y. Xia, C. G. Yan,
ACS Comb. Sci. 2011, 13, 436–441; d) J. Sun, Q. Wu, E. Y. Xia,
C. G. Yan, Eur. J. Org. Chem. 2011, 2981–2986.
[23] J. Sun, Y. Sun, H. Gao, C. G. Yan, Eur. J. Org. Chem. 2011,
6952–6956.
[24] a) E. Y. Xia, J. Sun, R. Yao, C. G. Yan, Tetrahedron 2010, 66,
3569–3574; b) I. Yavari, M. Sirouspour, S. Souri, Mol. Diversity
2011, 15, 451–456.
[17] a) V. Nair, C. Rajesh, A. U. Vinod, S. Bindu, A. R. Sreekanth,
J. S. Mathen, L. Balagopal, Acc. Chem. Res. 2003, 36, 899–907;
b) V. Nair, R. S. Menon, A. Sreekanth, N. Abhilash, A. T. Biju,
Acc. Chem. Res. 2006, 39, 520–530; c) N. Kielland, R. Lavilla,
Top. Heterocycl. Chem. 2010, 25, 127–168; d) A. Shaabani, A.
[25] a) P. Buonora, J.-C. Olsen, T. Oh, Tetrahedron 2001, 57, 6099–
6038; b) V. V. Kouznetsov, Tetrahedron 2009, 65, 2721–2750.
Received: December 2, 2011
Published Online: February 13, 2012
Eur. J. Org. Chem. 2012, 1976–1983
© 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
www.eurjoc.org
1983